Drastic Measures
by Featherstorm27
Summary: Cheren has been failing as a Pokemon Trainer and a rival, and is too broke to buy any items necessary for battling competently. He reluctantly becomes a prostitute to ameliorate his situation, but the job is not what he expected at all.
1. Chapter 1

Drastic Measures

Chapter 1: Fifth Time's the Charm! Or…not.

**Author's Note: First-person story about Cheren finding himself. The story really kicks off in later chapters, but these preliminary chapters build up the plot and develop character, [insert more literary malarkey here (jk)]. But yea, as the story goes on there will be yaoi and such smut, so just warning you now. Before it geT'S TOO LATE-**

**This is my first Fanfiction, so sorry if it's crappy or lame. But thanks so much for reading, and constructive criticism is totally cool too, man. But in other words, enjoy!**

**Also, I don't own any of these characters.**

"Go, Liepard! Show him your strength; give him your all!" I encouraged heartily, although my tongue was dripping only exasperation and hopelessness. This was my last conscious Pokemon. This was my fifth battle with my one true rival: the only trainer worth showing off to; the only trainer who could match my strength.  
However, I've been...slipping now, for some reason. How can it be, that Hilbert has three Pokemon remaining in this party, while out of my four only Liepard held up?  
The sleek purple feline stood on the field before his enemy, a dewott, with his head held high. Elegance radiated off his well-groomed pelt. But even his demeanor was a ruse, and under his confidence one could see tremors through stricken fur like a digging Drilbur forcing up grassroots. His pleading eyes glanced over at me; he was still tired from earlier on in the battle, when I had returned him after using fake out.  
"Liepard, use-"

"Razor shell, go!"

And in a heartbeat, Dewott was upon my remaining fighter, before I could even tell him to use fake out and prevent him from attacking in the first place! Or, wait...no...

Liepard was out like a light, toppling onto the field. His defense was weak, and I was relying on his speed, but...I guess so was Dewott. Nevertheless...I don't understand!

"Liepard! ...Liepard, wake up please! You can do this!" I hollered. The pain I felt caused my voice to collapse on itself.

"Uh...I dunno, looks like it's down for the count, Cher!" Bianca called out in her obnoxiously cheery voice, acting as the referee.

No...I just... "No! I don't believe it! I don't believe you're that weak, Liepard! There's strength within you!"

A low purr escaped from my Pokemon's throat. I was getting to him.

"Look inside yourself! You are strong! We are strong, together! We can make it- if only a little farther!" I shouted as the slender cat began to gain his footing once more. I was surprised my rival did not try to assault him or make any move to finish him off. Hilbert just stood there, hands on his swaying hips, watching on in interest.  
"Nothing can stop you if you have ambition, if you have vim!" I continued on, earning a subtle smile from Hilbert and a hushed giggle from Bianca. Glaring at the latter, I decided to ignore her. The matter at hand was more pressing. "Liepard, use fury swipes, quickly!"  
Directing his emerald eyes toward me, Liepard nodded his head once in understanding, taking on his confident battle stance once more. But the majestic cat simply stalked around his enemy slowly, still regaining his strength. Great, now he wasn't going to listen to me? Do I have to throw all my badges at him, I mean Arceus-dammit!

While I was cooling off, my spotted partner held out on his own, nonetheless. When Hilbert commanded his Dewott to initiate an aqua jet, my sneaky Pokemon twirled out of the way, and struck the otter from behind with fury swipes as he hit the floor. Fantastic! With outstretched claws, Liepard raged at Dewott's unprotected back, luckily striking all five times and even getting a critical hit! I fist pumped the air in excitement. With all the EV training in attack my Pokemon has been doing, he was able to knock out my rival's partner with just the one attack! Hilbert gasped his surprise, perhaps stunned by the elegant carnage that just took place. But he soon hardened his gaze, and returned his fainted Pokemon only to send out another.  
My confidence faded. I was worried. My rival had two Pokemon left, and the eager Gurdurr he sent out was still at full health, not having been used until this point. My Liepard's green eyes widened, slits dilating. Now he REALLY looked over to me in despair. He had a type disadvantage, and on top of that, there was no way he could survive a hit from Gurdurr's thick metal beam.

Hilbert played with his pokeball, tossing it in the air without a care in the world. "Like him? Just evolved him the other day, and he's ready to show off his new power!"  
Well of course he was. He's got a steel beam taller, and heavier, than your fucking body.

Nonetheless, "Well, mind you, it's not over yet! Liepard and I will show Gurdurr just what the ideal level of power is!" I rebuked, and tried my hand again at fury swipes, having run out of potions earlier on.

Disastrous. It only hit thrice this time, and barely ticked his foe. "...Shit." I muttered under my breath as my Liepard jumped away from his enemy. In my blind desperation, I forgot just how naturally defensive Gurdurr actually are.

I gazed on in stunned dismay at the scene. Hilbert's mouth moved, and soon enough, Gurdurr dropped his beam and lunged at my poor Liepard with some sort of open-handed slap (which I assumed to be a wake-up slap). He was down for the count.

The knocked-out feline was launched in a direction near me. In the heat of the moment I dashed toward his destination, catching him in my arms. But, alas, my body was thin and petite, so the impact force made me topple down to the floor with the large cat. Oh well. Almost breaking my rib cage was definitely worth saving my dear Pokemon from suffering any more pain than he already had.

"GOAAALLLLL! Nothing but net; great catch Cheren!" Bianca exclaimed, louder than a siren. "And a fabulous victory goes to Hilbert!" She added.  
Arceus-dammit...how I've grown to hate those words.

With a sharp intake of breath, I gently released my hold of the spotted purple feline. "You fought amazingly, my dear friend." I whispered into his unconscious ears, and returned him to his ball. "Get some rest." I added quietly.

The crunching of grass and dirt under feet scared off the tranquility. When I looked up, I noticed Hilbert standing over me, offering me a hand. "Gosh, you alright, Cheren?" he asked, concerned. "That was some fall you took there!" I seized his hand, wiggled out from under Liepard, and lifted myself up off the ground. But my legs buckled and I fell into his arms, too breathless to reply.

"Hey..hey Cheren," his voice drifted in and out of my consciousness. "You alright?" He asked, pushing me off of himself and trying to stabilize me on the ground before us.

I held my place. "Y-yea, it was just my cat. It'll take more than that to take me out." I slurred, massaging my temples.

"Oh, great! And that was really cool what you did there! Encouraging your Liepard and catching him from a fall. Like some kind of Pokemon superhero!" He noted childishly, his being radiating with energy. I sighed and rolled my eyes, still breathing hard. At least I could impress him even though I lost. With a chuckle, my rival extended his hand out to me. I took and shook it, to which he responded with the brightest of smiles. "But really, you totally did awesome! Two to one- not too bad." Hilbert complimented.

"Well, you too are strong, as usual." I replied, trying to hide how defeated I felt. All of my strategy, all of my hard work into using type advantages, Effort Value training, and hold items to out-do my enemies; proved futile in defeating my rival.

"Alright, quit the chat!" Boomed a familiarly rowdy voice. "I call winner; Cheren, you be referee this time!"

Hilbert laughed. "Bianca, dude, our Pokemon are tired as hell! We need to head over to a Pokemon Center ASAP!"

"Hey- no, wait!" She grabbed two pokeballs and stomped over to the field. "Two on two- you have two left, right?" She demanded.

"Uh..well yea but Tranquill is only half health. I returned him earlier on in the match, remember?"

She pouted. "Aww, boo. Fine, let's go- but quickly! I'm so pumped!" She put away her pokeballs and ran off to the nearest town in a heartbeat. Hilbert and I glanced at each other with amused smirks and rushed to catch up.

The wind flowed through my hair, and ruffled the grass on the field. After my team and I rest a bit, I would have to figure out why in the world I could not defeat Hilbert, not even since day one of my journey!


	2. Chapter 2

Drastic Measures

Chapter 2: Feelings Jam

After Hilbert and I fought on Route 5, we sped over to Nimbasa city to quickly heal our Pokemon. Upon returning to our area of battle, we were prompted by Driftveil city's gym leader to remove a Team Plasma threat in his city.

Although I was able to show my strength against those ne'er-do-wells and we fought them off without a problem, I knew there was something amiss. My previous loss against my true rival was still bothering me. I'm sure it hindered my performance too, because I committed even more silly slip ups. Why would I utilize Servine's leaf tornado against a Tranquill...and even send him out to fight a flying type in the first place! What in the name of Arceus and Mew was I thinking? Was I even thinking?!

I cradled my head in my hands and kicked the dirt below me. The bench I was sitting on creaked. What the hell was going on with me? This wasn't even the first time I slipped up. I've even lost some random trainer battles, and had to fight Elesa twice just because my strategy was wrong, and I was too distracted by my previous loss with Hilbert.

At the first loss I brushed it off. Both our Pokemon were level five and only knew tackle. We were equally matched, so it was just whatever. I would EV train my Snivy later, catch some more Pokemon, and EV train them too. I would use the strategies I learned in school and researched online to prove to those damned schoolyard bullies and everyone else that I wasn't just some weak, nerdy little kid. That even I could be strong, that I could gain all 8 gym badges, that I could surpass victory road, that I could face and defeat the Elite Four and the champion, Alder. No one would stop me, not even the toughest, most competitive trainer in the world tournament!

And everyone expected that to happen. With my knowledge, I gained a sort of reputation around my school and with my friends. Hilbert and Bianca looked up to me when we were too young to have Pokemon. I would teach them what I researched, and they held me as some kind of genius or master trainer. Whenever we battled with poke dolls or our parents' pet Pokemon, I always knew what to do, and always came out on top.

But now...I couldn't even beat Hilbert once, not since the start of our adventure. And it's been seriously getting to me. I was supposed to be the powerful one! I was supposed to be the-!

One of my pokeballs wobbled. I released the Pokemon within. Servine jumped up onto my lap and took his seat there like a spoiled puppy. He was pretty heavy, but I was used to it.

I sighed, and carressed his grassy scales. He had a tendency to act like this all the time, as if he were a house pet and not a fighter. But I wasn't complaining. I needed to calm down anyways, and think things over with a rational mind. Clear my conscience of all my...dare I say...disbelief of and jealousy for Hilbert.  
Servine purred a soft hiss, blinking his eyes shut in enjoyment.

I smiled. "You know you can't do this when you're a Serperior, right?"

The Pokemon looked up at me and cocked its head over to one side.

"Don't act so oblivious. Do you know how heavy you'll be when you evolve?"

The green snake pouted, and smacked my arm with his leafy tail. I raised my hands up in mock shock. "Hey, I'm not lying am I? I'm sorry you're so sensitive about your weight, but in a couple more levels you're gonna gain a lot of pounds, you know!"

Servine flicked his forked tongue at me, and jumped off of my lap. He padded over to the railing that separated this street from the lake surrounding Driftveil. The stars shining in the indigo sky above burned themselves into the water's rippling surface.

Around this time of night, Hilbert and Bianca were probably doing their own thing: sleeping, eating, training, whatever. But I found I couldn't do anything of the sort. I was too pensive to rest, too broke to buy an inn room or food, and too confused to fight.

I got off the bench and stepped over to where Servine was, wrapped around the railing and staring at that gorgeous, picturesque scene. Following suit, I placed my elbows against the railing and appreciated the night. Absorbed the tranquility into my very being, I tried to clear my head. But like a ghost's curse, my woes weren't going to leave me so easily. I sighed. "Damn, Servine. I have to figure this out."

The grassy reptile ripped his eyes from the scene, surprised to have been referred to.

I lowered my eyes to the glimmering water and continued. "What's wrong with me, Servine? Why am I slipping? Why can't I defeat Hilbert?"

My partner frowned and swished his tail side to side, gesturing with his hands. I'm sure if he had larger shoulders he'd be shrugging them.

I sighed again, turning toward him. "Am I just...too weak?"

Servine looked up pensively, pondering the thought. He shook his head side to side.

"Ok then...am I not strategic enough?"

Servine blinked, and then smiled. He tossed around the Sitrus berry hidden in his tail to show it to me.

I grinned weakly at the implication. "Well, yea, there's that. But...is that enough?"

Servine rolled his eyes, and growled a bit with his name. "Ser! Ser! Vine!"

"Ok, ok, geez. I guess I'm just missing the bigger picture of what you meant."

The Pokemon nodded.

"Yea. I guess...no, of course, I do have strategy. You're right, Servine. Why do I doubt myself so damn much? It's the reason why Liepard is the first on my team with fake out, and overwhelms the opponent with his attack. Why Panpour is there to weaken my enemy and even deal heavy hits. Why you and Tranquill not only deal the final blows with your enhanced special attack and attack stats respectively, but also are able to heal and defend yourselves if necessary. Any other obstacles and unexpected circumstances are easily conquerable by my, and all of your, quick-thinking and resilience. So...what's the problem with me, Servine? Why can't I focus anymore; why couldn't I react to Hilbert's Gurdurr in a suitable manner?" I clenched the rails, growing irate as I reiterated. "Why can't I defeat my rival?"

My Pokemon tossed his verdant head side-to-side, musing it over. He looked down at the street for a good moment, then at the lake again, and then at me. "Ser...viiiiinneee." He mumbled, looking me over. He focused heavily on my eyes and frown, interrogating my visage for answers. "Seeerrrr...ser..VINE!" He exclaimed, and danced around a bit, flapping his leafy little hands in the air.

Getting closer to me, the serpentine Pokemon tapped my head with his tail, clapping and nodding in approval. It was always a game of charades when communicating with Pokemon. But you get used to it, understanding their implications. "Something about my head...symbolism...perhaps my brain?"

"Servine!" He waved his leafy hands in the air in an arc. "Ser! Ser!"

"Yes...it's amazing, perhaps? I mean, I'm not trying to brag, I'm just interpreting."

The snake Pokemon nodded. Then he put his tail to my chest, on what he probably intended to be my heart.

"My heart...what about it?"

My friend nodded once, and then continued by swishing his tail away.

"Hmm...my heart's...gone?"

He urged me on to a better conclusion with a wave of his hand.

"Erm...my heart's...not into it, perhaps?"

The snake gasped and nodded; I had hit the nail on the head. I pondered the thought. "Really? Elaborate. What's my heart not into?"

My Pokemon pointed to himself with his hands. Then he pointed to the other pokeballs along my belt. "Wait...what? How is my heart not into you guys? I plan out every battle according to your strengths and weaknesses, I consider your individual skills, moves, behaviors, and abilities, I-"

Servine shook his head and slapped my arm with his wide tail. "Ow, hey! What?! What am I missing?!"

He pointed to his own heart. I frowned. "Arrggghhh..what do you...I don't understand!" I massaged out the wrinkles on my angry forehead. "Never mind. Let's just take a walk." I grumbled, pushing myself off the railing. Servine jumped onto my shoulder, causing me to flinch and wobble for a second until I could get used to his weight. While my brain was trying to process all of these new conjectures, my feet wandered along the dark, paved road. Before I knew it, I was back on the Driftveil city drawbridge, muttering ideas and things that would get me nowhere.

"How can my heart not be into you guys if I trained you and raised you from the very start?!" Arceus, bless Servine for putting up with all my rambling. "I'm not so bad at this...or, am I? No- of course, that's it! I'm so scatterbrained, I'm such an idiot! Why was it that after I sent out Liepard to face Hilbert's Dewott earlier, my first thought was to make it use fake out?! That would've failed anyways because the first turn was long since over! Arrrggg!" 

Soon enough, I had reached Route 5 again. A few musicians there looked over to the raging teen who stomped along the ground like a Tyranitar and yelled into the open air. But they eventually ignored him, and, like Servine, left him to figure things out for himself.


	3. Chapter 3

Drastic Measures

Chapter 3: Nimbasa, Su Casa

Once my scattered brain could comprehend where my furious feet had taken me, I calmed myself down, and took a grateful look at my destination.

There was something beautiful about Nimbasa at night that just relaxed me, inspired me. Sure they can call Castelia "the city that never sleeps," but in comparison, this electrified city was much more exhilarating and lively. On one side of the city, one could hear the mellifluous tunes of the Pokemon musical pouring into your ears. On another side, one could hear the excited squeals and jubilant laughter of children and families in the amusement park, braving vicious roller coasters and the height of that magnificent Ferris wheel. And just nearby, one could catch a glimpse at the fun and fashionable Nimbasa city gym, whose owner was not only the symbol of modeling and Unova fashion, but also a shocking opponent. And just below, one could feel the tremors of those subterranean steel monsters of innovation, a fantastic combination of modern technology and the ancient Pokemon tournament: the Battle Subway, where new meets old. These, along with many other notable features of this vast city, come together to make Nimbasa the number one most exciting place to go for anyone in the Unova region, and even abroad.

I sighed pensively, admiring the allure and brilliance of this marvelous city. Upon landing in Nimbasa, anyone might feel obliged- compelled, even- to take action in one of its many centers of entertainment and competition. I, however, am usually just enthralled by the landscape, and the many people within it who wish to do just that. Like Burgh or any other artistically-inclined fellow, I primarily enjoyed being there and watching the sights. With Servine draped around my neck in slumber, I ambled around the bustling city, too engrossed in my surroundings to let my unresolved conflicts consume me further.

Children dashed around yelling while their parents desperately tried to keep up. Couples wandered aimlessly, enjoying the presence of their significant others and discussing the events of their dates (and no, I wasn't...that jealous). I took in all ambient sounds to fill my ravaged mind with fresh stimuli and new thoughts. Servine, however, received them less than happily, and hissed under his breath. I laughed. "Would you like to sleep in your pokeball?"

The snake snorted and hissed. "I'll take that as a 'no?'" I asked, teasingly. The grassy snake just huffed and went back to sleep.

Humming against the smile on my lips, I took a seat at an amusement park bench. I couldn't believe this place was still open and running- it was a quarter to ten, for Arceus' sake! I noticed a woman sweeping up trash on the floor and depositing it in a garbage can. Those poor employees, having to work so late. Hah. Reminds me of how I was job hunting just recently.

I was broke. Pretty much flat broke; all I had in my pocket at that moment was 1286 poke. That was barely enough to pay for potions, berries and other hold items, and pokeballs, let alone a meal or an inn for me. I was losing money on quite a few failed trainer battles, and because I was running low on funds, I figured trying out for a job wouldn't hurt. In just the last week I've offered my services for the role of a human or Pokemon daycare assistant, a waiter, a Poke-mart cashier, a receptionist for some businesses, whatever I came across; and turned in applications for those. But most of them hadn't called me back, and mainly because I was rather young. Most businesses favored applicants who were at least a bit older, and even more so if they were experienced, although there was no law for a minimum working age. It was probably just a responsibility or wisdom factor that most believed came with age. That was probably garbage though, and I could work just as well as, if not better than, someone a bit older than me! (I'm placing my bet on higher child liabilities. Fucking government...).

I sighed. If only I knew the risks of becoming a Pokemon trainer beforehand. I can't go back home and crash at my mom's place because I don't have fly, and I can't just pull money out of my ass. Dammit. What was I thinking when I set out on an adventure to become a Pokemon master? That life would be entirely easy for me, and I could just get whatever I wanted, whenever I wanted it? Bianca's dad was right; this career path was a pretty unreliable and even dangerous one to chose.

"Wait- what am I thinking?" I asked myself in a stern tone, causing Servine to rustle a bit. I put my head in my hands; why did I find Bianca's father's words credible now when not a few weeks ago I had blatantly opposed them? "Argg...if only I were more focused and trained better, I wouldn't have to undertake this argument with myself!" I muttered under my breath, so as not to ruin the ambiance or wake my partner up with senseless babbling.

I was done with that soon after; I needed to focus on the future and what was truly important, not dwell in the past. I got up and wandered around the park. Perhaps I could apply to work there as well. I went to a ticket booth and asked where I could go to do so, and the guy there, whose eyes were about to fall out from exhaustion, pointed to a small building behind me labeled "customer service." Then I went there, filled out an application to the best of my ability, and gave the paper back to the lady at the desk. She took it and nodded, saying little "alright, ok," phrases here and there, and put it in a file. "Thank you, um…Cheren was it?" She asked. I nodded. "Yes, well we may not hire you at such a young age but-" oh, Arceus, there we go again. "-don't be discouraged by that. We will consider you anyways the next time we look for someone to hire. So thanks again!" She said with feigned cheeriness, and waved. I smiled formally, and put out my hand for her to shake it. "Thank you, miss." I replied.

"Oh it's no problem." She shook my hand firmly, then let go. "Oh, and nice scarf you have there!"

"Hm?" I looked down at my Servine. His torso was draped around the front of my neck. "Oh, this? It's real."

The lady looked at me, bewildered. "What? You mean it's made of real skin and scales?!" She exclaimed, assumedly teasingly.

I chuckled. "No, no, I can assure you...they're just molted!" I joked, following suit with the drama.

The lady gasped. "Oh my- you criminal!" She clapped a hand to her cheek in mock surprise. We laughed it off, the vibrations of my throat waking Servine up once again. With another huff, he slapped my face with his tail and tried to go back to sleep. The woman cracked up again, noting how "sassy" my Servine was.

After the friendly banter, I waved her goodbye and took my leave. Walking out of the building, I felt something odd. Perhaps...a pair of eyes on me? Figuring it was a trainer wanting to battle, I grabbed Liepard's pokeball reflexively and took a gander at my periphery. No one, not even shadows in the bushes. Maybe I was just being paranoid.

That is, of course, until a hand grabbed my shoulder.


	4. Chapter 4

Drastic Measures

Chapter 4: Probably Should've Ran

The cold hand brushed against Servine's grassy scales. Suddenly on the defensive, my partner bit the hand reflexively, noting it came from an unknown source. I turned around to face the person while my trusty Pokemon jumped down from my neck and took a stand, hissing venomously. The person- who was skinny and pale yet still recognizable in the dark as a man- was clutching his hand in pain, but made no sound to show it.

I hesitated. Although he was wearing a nice suit, he...really didn't seem like your average guy. I took a few paces back. Should I run or...-

I froze. When he looked up at me in contemplation, I was petrified by his unnatural eyes. Bright, piercing gray orbs that held me in place like some sort of Deerling in the headlights. And his voice just piled on the pressure. Loud and stern, yet attempting to be friendly, at least. "Sorry if I scared you, there, kid." He apologized, standing up straight, walking closer to me and into the light of a street lamp. He was tall, and had long, well-kept white hair. By his business-like attire I could only assume how rich he was. Hopefully that meant he wouldn't rob me.

Servine was still blocking his advance. I could've just ran, and my Pokemon would catch up. Yet...something told me that this guy was probably not much of a threat. Maybe he had someplace to go and just bumped into me. "Uh- erm, no you're fine." I replied timidly, then took a deep breath to regain a little more of my confidence. "I'm just worried if my Servine scared you or not as well. You hurt?" I asked.

He laughed ominously. "Ha. Ahahah...no. That was nothing." He looked down to the floor, as if he were pondering something. "Hmmm...perhaps I'll just cut to the chase." He muttered audibly enough, and then turned over to me. "I see you're looking for a job?" He inquired, stepping a little closer.

Servine hissed again, but I waved him off, curious. "Uh...yes, how do you know about that?"

"I overheard you ask that man at the ticket booth."

I frowned. Was this guy...stalking me? Fuck, I did need to run. "Oh, well yea, I am. But I've applied to a lot of places already so...I'm not interested in…erm, whatever you have..." I replied as I began to back away from the shady man.

The man huffed, and began to raise his arms but restrained himself. He sighed and walked closer. "W-...why not?" I could tell he was shaking slightly from anger. "You have yet to hear what I have to propose."

I still shook my head, and my feet ached to run, already retreating. "Yeah, no it's fine, really! I'm not interes-"

"I'll pay you handsomely."

I stopped. "You will?"

"Yes...not to mention you'll get tips." He sized me up. "And by your looks I think you're quite capable of this job."

That got me thinking. What kind of job was it if I got tipped AND paid at a high rate? Doesn't sound like a regular waiter or deliveryman to me if it relies on something as vain as my "looks," either.

Maybe it's something...more vulgar? I shuddered at the thought. "N-no...no that's fine. Again, I'm not interested."

"You haven't even heard what I have to offering yet." He shot back coolly.

I sighed. He did have a point. Perhaps I was just jumping to conclusions? "Ok, what is it?"

He looked down at the ground in contemplation for a while, staying silent.

"Um...are you going to tell-" in a sudden instance of betrayal, my stomach growled. Damnit. I hadn't eaten since this morning.

The man seemed to be smiling, gray eyes glowing brightly; a pale crescent and stars against the darkness. He looked up at me and chuckled quietly to himself. "Would you like to discuss this over dinner? I take it you have yet to eat."

At the mention of food my attention was drawn. But...coming from this guy? "Uh...apparently so."

"Would you like to accompany me to a restaurant to which I was heading? I'll pay for you, seeing as you're broke."

"W-what?! Why would you think that?" Dammit, how did this guy know so much about me?!

"Why else would you be job hunting?"

"For...honest reasons."

"A Pokemon trainer? I doubt it." He sidestepped Servine quicker than I could blink, and when my eyes opened he was grabbing my hand. It felt slightly cold to the touch."Come now, it's a really fabulous place. I can elaborate on my proposition over there."

Well, I couldn't back out now, since he was practically dragging me (damn, he was strong). I picked up my feet and walked normally. Servine confusedly dashed to catch up, glancing up at me with a face that asked, "What? Is he safe now?"

I nodded warily, and he ran and jumped onto my shoulder. He glared daggers at the suspicious man, nonetheless.


	5. Chapter 5

Drastic Measures

Chapter 5: _Seriously_ Should've Ran

"Wow- this is actually pretty good." I stated, taking a bite out of the meal I ordered. Some kind of berry salad with poultry. I was eating light so as not to be too much of a burden.

The man, who told me to call him "Umbra," nodded. "Heh...I didn't know I was treating a food critic."

My cheeks grew red in embarrassment. "What? Er, no I've never been here, so I wasn't expecting- hey, wipe that grin off your face!"

"Hmm? Why? Can't I admire how cute you are?" Umbra asked with a smirk befit of Giratina itself.

Now I was really blushing. "W-wow that was fast. All this talk and not even a ring?" I joked back (hopefully assuming what he had said was indeed a joke).

Still smiling, the white-haired man stared at me through hooded eyes. "Hmm...a sense of humor. Lovely." He mumbled to himself, though audibly enough to be heard.

This guy was definitely creeping me out. After dinner I was planning on making a run for it (If he tried to catch up, my Pokemon would sure make him regret it). And that kind of flirting wasn't his first offense either. He also held onto my hand WAY to intimately for my liking on the way here, and noted how well my skinny jeans complimented my legs, among other things. And I wasn't dense either. I could only assume that the job he had to offer me would be...well...THAT kind of job. A job that I definitely wouldn't argue against being too young for.

But to be honest, I couldn't say he wasn't...rather charming.

Oh perish the thought! Arceus-dammit, why was I thinking like that?! I looked down at my Pokemon, who all were eating happily and voraciously (this Pokemon-friendly restaurant let Pokemon eat free as long as the customer ordered something! That was pretty nice). Looking at how he's treated us thus far, I felt guilty for wanting to ditch him. He didn't actually do anything to hurt or take advantage of me.

But...that didn't mean he wouldn't later. I looked back up at him, continuing to nibble on lettuce. It seemed like he had been staring at me for all that time, but he quickly looked elsewhere to hide it. He took a bite out of his food and went back to talking to me as if none of this ever happened. "So...just out of curiosity, how long has it been since you've eaten last?" Umbra asked.

I shrugged. "This morning. It wasn't much either. Just a sandwich, but whatever. I'd rather feed my Pokemon first, and make sure they have all the potions and items necessary for them to fight better. Wouldn't be a good trainer if I didn't."

The well-dressed man before me nodded. "Really? How noble of you. I'm sure they appreciate that."

"Yea. They're my friends. Gotta look out for them." I mumbled. In the span of us talking, I had finished my small meal.

"Yes. Well, now that we're all satisfied," he remarked, referring to his Pokemon being fed as well. "Have you been considering my offer, Cheren? From what I've told you, at least." He asked. That was fast. I guess he wasn't one for small talk.

"Um...yes, somewhat." I lied. "Care to tell me what it actually is, now?" I asked, demanded almost, although I didn't intend to be so blunt.

Umbra, seeming slightly nervous, took a deep breath. "It will only be a night job, probably starting at six, but orientation will be an all-day thing until you get the hang of things. For you, I'll give 30% of all commissions, plus you can keep whatever clients tip you..."

"Alright, wait!" I snapped, brows furrowed, but still kept my cool. "Tell me the job first before you go into details."

He frowned, looking down at his plate unsurely. He swirled whatever was left of his food around. "Well...heh...I don't want you to say 'no.' I'm trying to make this as convincing as possible for you."

Doesn't matter, I thought to myself, I was still going to deny him anyways. Probably. 30%? That's Tauros-shit. And he was acting way too shady for my liking. "That's fine, but I'm not going to say 'yes' without knowing what the job is, at least."

Umbra sighed. "Well...yes, of course...I have to spill it sometime." he cleared his throat. "I'd like you...to be..." He began nervously, dragging it out. I held my breath, practically on the edge of my seat in curiosity.

He came closer to me. Finally, he whispered so as no one else could hear:

"A prostitute. For me."

My eyes grew wide and my stomach churned. Well...that wasn't...unexpected, considering the way he's been judging my looks all night. "Wait...w-what do you mean?" I asked, although I definitely shouldn't have.

He sighed, irritated now. "I'm a pimp." He continued in his hushed tone. "I have a good amount of males whose bodies I sell on a daily basis for the pleasure of others. I want to hire you to do the same." He clarified. I guess he was tired of sugarcoating everything. "What do you think?"

"I...um..." I swallowed my saliva. No wonder why this guy looked rich. He probably was. "I...d-didn't know that could happen."

Umbra chuckled. "Don't be so naive, please. Humans crave sex, so they buy it." He said matter-of-factly. The ease of which he did made me feel so nauseous.

"I-I guess b-but...w-with...men?" I never knew women got horny enough to hire male prostitutes.

"Yes. Men can be prostitutes, if that's what you meant. For the love of Arceus, Dialga, and Palkia, Cheren, how old are you?" He asked rhetorically.

"Um...well...too young for that job." I growled, not willing to give out such information to a stranger.

The long-haired man cast a bewildered look to me. "Oh...shit, really? You look...so much older. But no matter. Would you like the job or not?" He asked.

"Uh...isn't this illegal, though? Since I'm so young?"

"Hah, hell yes. Prostitution is illegal no matter the age. Doesn't matter to me, though." He shrugged, pausing for a second.

"Well, I take it you'll need time to think about this. But I seriously suggest you take my offer. Jobs are hard to come across nowadays, and I promise you this one will pay well. And, who knows, you might actually enjoy it?" He suggested with a wry smile, and then continued eating his meal.

Out of all the things I could've possibly been asked to do, this takes the icing off the 'worst' cake. I know I should've denied it and just ran or called the police, but...why was part of me considering it? I don't even care for sex; I'm platonic for Arceus' sake!

"Hmmph..." I put a hand to my head. Looking down at my Pokemon, I noticed that some had finished eating and were talking to each other. Servine looked up from his bowl and glanced at me.

I guess it's the part of me that's just eager for adventure.

Later on, the waitress came by to take our plates and give Umbra the check, which he paid in cash. It had grown quiet between us as I mused over the man's request. When the waitress finished her business and left us alone, I sighed deeply, and gave him my answer.


	6. Chapter 6

Drastic Measures

Chapter 6: As the Sun Sets, the Moon Rises

**A/N: Hold on to your underpants, guys, this is where the progressively becomes less and less tame! Thanks so much for reading up to this point, and if you could also tell me how you think about my writing style that would be cool too. The way I write has always been iffy to me, so getting multiple perspectives on the topic would be totally awesome. Thanks, and enjoy!****  
**  
_This was a very valid choice_, I thought, beginning to actually regret it as I made my way through the more derelict streets of Castelia city. _Very valid; my reasoning is flawless_. Words reiterated like echoes in a cave, pervading my consciousness as I hit the road that was my destination. Shale Street, a bolded sign read. Cars sped by me, and businessmen pushed past me on their way home.

But when I walked onto the street (which was more like a horribly-lit, sordid alleyway, honestly), no one was around. Save for scavenging Rattatas and Purrloins. I surveyed the area, hoping I wouldn't get robbed, clutching my Liepard's pokeball and the address of Umbra's workplace with a trembling hand.

A cool breeze wafted by, chilling my body, making me shiver even more than I already was. I almost dropped my pokeball. _This was a very rational choice_. I reassured myself over and over again, to the point where it became incredibly annoying. I slowly made my way to the right building: "154, downstairs, C," I verified on the notepaper. I gripped the railings. Of course this was a smart choice; I didn't need to run like I had promised myself I would. I had been job hunting for the past month then, and no one had called me back. And with each passing day, I was only getting more and more broke, especially since there weren't a lot of trainers around to defeat.

And this job couldn't be too hard...right? Just go place to place having sex with women?

I sighed, and steeled myself against the cold. I was scared, nonetheless, but I was determined to make this work. It was probably my only chance to further my career as a Pokemon Trainer. I descended the steps and knocked on the door at the bottom. No answer. I tried my hand at the thick metal door, and with a strong tug I yanked it open. It shut behind me as I took a few cautionary steps inside, as if to mark my fate.

I took note of my surroundings. Just a long stretch of hallway, trapping me on each side and poorly lit save for one ceiling lamp. It wavered slightly, producing an eerie creak to the likeness of a Murkrow's squawk. Inhaling another deep breath, I made my way down the hallway. My shoes creaked against the old wood paneling and echoed along the walls.

This was beyond unsettling, like staring into the petrifying gaze of a Seviper or Galvantula. Delving deeper into the darkened walkway, I could see a couple of doors scattered around. Building C was located at the end. I knocked on the door with a still shaking fist.

The door creaked open. "Hey. You're early." Umbra noted, opening the door and leaning on the frame, arms crossed. He flipped his long, silky white hair off his face. This time he was wearing a white tank-top that fitted his body well, showing off his muscular chest and arms. But...erm…it's not liked I cared for that kind of thing anyways.

I rolled my eyes, trying to hide the fact that my face was slightly flushed. "Tch. I believe 'prompt' is the word you're looking for."

Umbra chuckled. "Whatever floats your boat, kid. Anyways, step right in." He grabbed me roughly by the shoulders and pulled me inside. It was dark and empty, save for us. As the man shut the door, I inquired, just out of curiosity. "Where's...everyone else? I thought you said you have more prostitutes?"

Umbra shrugged. "They don't work here. This is just my actual house." He said, turning on a light to reveal a studio-like room. "Well...more like my living quarters adapted from an old building. And I don't keep my boys here like slaves or some shit, unless they don't have a place to live and want to crash here at night or during day. I let them do what they want during the day, and whenever I have a job for them I give them a call and send them the address. It's quick, easy, clean. No one has to find out, no one has to rat me out- I'm happy, the boys are happy. I'm not corrupt, selfish, or overblown like those pimps you see in the movies or hear on the Internet. It's an honest business. An ideal business." He went on, hitting it home with his strange morals. It reminded me of something...someone, perhaps. "...Anyways, that's how it works. None of my boys work for me against their own will. Some want to make money, others want their fix. Whatever it is, they're happy, and I'm happy." He reiterated sternly. It seemed like he was convincing himself of this more than telling me it. "And that's how it will be for you too. You can train your Pokemon during the day, but at night you do your job."

I nodded. It wasn't my place to point out the kinks in his logic. "Okay. So...what exactly does my job entail-" he shut my mouth.

"Shh...no more questions. Time is precious; let me do the asking." He growled, removing his hand from my face.

"I...Er-..okay."

He cleared his throat. "Alright! Well, let's clear this up now. First question of orientation is: what is your orientation?" He asked in a more cheery fashion.

I blinked. What...kind of question was that? I frowned, lifting up my sleeve and glancing at my watch, which had a built in compass for the avid adventurer. "Um...south-southwest."

Umbra's smile turned into a frown. He shook his head in disdain and laughed eerily. "Oh sweet Arceus...no, your SEXUAL orientation."

"Oh...OH, I apologize." I blushed in embarrassment. "Um...I'm not entirely sure. I've never put much thought into that."

"What gets your dick hard? That doesn't require any thought."

"Erm...well...nothing! I don't know!" Oh Mew, he didn't have to be so vulgar about it! "Why is this even important? Aren't men supposed to like women or something?!"

He sighed, mumbling something about "stupid traditionalists". He pulled out his cell phone and pulled up a picture to show me of a naked woman in a seductive pose. I frowned. "Hard?" He asked, bored.

I looked at it for a while, not sure of whether or not I should even be seeing it, blushing still in mortification. "Um...sort of?" I asked while he unzipped my pants and grabbed my privates all of a sudden. I flinched, having never been touched there before. "ACH! WHY-?!"

"Yea. Half-chubbed." He droned, and flipped to a picture of a rather muscular, naked man, also in a seductive pose. My face burned red at the sight of it. I had had enough, and pushed the image from my view. "EW...w-why would you show me _that_?!"

He laughed, and forced my hand down so I could stare at the picture. I couldn't lie and say that the man wasn't attractive (or dare I say it, sexy) but...why was I even thinking that way about men?! Umbra checked my erection again. He smirked. "Heh. There it is. I'm thinking that maybe you're hiding something, Cheren."

"What?! N-no...shut up!"

Umbra laughed heartily. "Nah. Anyways, you're probably bisexual, which is a good thing, for you at least. One guy I hired was straight and I had to fire him because he couldn't handle-"

"Wait, what? I thought the clients were women!"

At that, Umbra snickered, then let out a wicked, booming laugh, slapping his knee even. When he calmed down, he clarified. "Ahah...ha...no. I only cater to men. It's more fun that way."

"Eh-...exCUSE me?! You mean to say t-that...what?! How does that even work?!"

Umbra was now making his way over to another room, dragging me with him. "What do you mean?"

"How do men have sex with other men?!"

We stopped in what looked like his bedroom, and he threw me onto his bed roughly. Then he burst out laughing. "Ha ha…wow, you really don't know? You are one sheltered kid. It's through the ass."

My mind was reeling and retching at the thought of it. "Through the- whAT? I thought that was just for defecation! Doesn't that hurt?!"

Umbra shrugged, looking annoyed. "It is, and it can, if you don't use some kind of lube." He walked over to his closet and began looking for something.

"What the heck is that?" I was exasperated. I had just learned so many new things that day which I honestly did NOT need to learn.

"Hush. I'll tell you all about the nuances of anal sex later. Next question: you have a Tranquill, correct? From yesterday night? Does it know fly?" He asked, pulling out some strange looking objects from his closet.

I shook my head, which was completely agonized at that moment. Could I even endure this kind of intercourse? "Yes and no."

He tossed me a cartridge, which I barely caught. "Then here. Teach it fly. It makes finding your clients so much easier, and my business so much more regional."

I frowned. Fly wasn't the best move to teach a Pokemon. Although powerful as it was, Fly was a useless two-turner made useful only if the Pokemon was holding a power herb. Nonetheless, I didn't have a choice here. "S-sure. Now?"

"No, later." He got up and smirked, holding one of the lengthy objects. "Now I need to educate you. And by the sound of it, I'm going to have to start from square one."

I swallowed the saliva which was threatening to choke me. After taking a good look at them, I now realized those objects were penile. I shuddered. This was going to be a _long_ night.

And that man would _not_ stop smiling!


	7. Chapter 7

Drastic Measures

Chapter 7: Oblivious

I stared down at the shiny, pink-colored object in my hand (a 'dildo' he called it) with a bored look on my face. Having been handed a bottle of lubricant, I squeezed out its contents into my palm and applied it sparingly to the shaft and head.

In the span of a week (my employer spared me by making my orientation a nightly deal), Umbra taught me a significant amount of information about man on man intercourse. Oral, anal; even put your hands and feet in there. Excluding BDSM, kinks and fetishes (Sweet mother of Mew, why do those even exist? I hoped to Arceus I would never have to do any of them!), gay sex didn't seem as bad as I thought. Doable, and even slightly interesting, but probably rather uncomfortable. Although Umbra told me the prostate acted as a 'pleasure spot' when prodded and rubbed up against, I didn't believe him. He probably just made that up to make anal seem enjoyable.

Oh well. I'd find that out on my first commission, Umbra told me. He didn't want me to "loosen myself up" just yet with a dildo or my fingers. So for now, I would have to suck it up and practice the…extraneous activities. And that was the awkward part. Stuffing long, rubbery toys down my throat was agonizingly uncomfortable, no matter how much cherry-flavored lubricant the skinny asshole slathered onto them (in fact, the lube made it twice as gross). While doing so, the pimp taught me how to slide and press my tongue against all the right spots when 'blowing' someone, how to repress my gag reflex, and how to swallow a man's semen without spilling a drop. He even gave me pointers on how to properly tease a man. Kiss and nibble on their lips and neck, pass your tongue along their nipples (pretty girly if you ask me), caress their thighs- just your run of the mill stuff!

I snickered, lifting my mouth off the fake genital I was lavishing. If it was one thing, Umbra's leniency towards the whole matter was hilarious. He treated cross-dressing and bondage like one would a tranquil walk with your Lillipup around the park. I wouldn't say it helped me become more comfortable with all these new, wacky ideas, but it did make me feel less pressured and less nervous than when I had first accepted the job. In fact, I might as well have been desensitized to the fact that I would soon be selling my body to other men. I remembered coming to that realization earlier in the week and just shrugging. Couldn't be that bad. Just an idea in the back of my mind, now.

A calm, yet rather labored voice intruded on my thoughts. "Why did you stop?" Asked the white-haired man, sitting on the opposite side of the bed, trying to hide the fact that he was anxiously rubbing his crotch. He watched me like a Mandibuzz would her dying prey.

I shrugged. "I...erm- well, this is just pretty ridiculous to me."

"Oh? Why so?"

"It's rather awkward. All I'm doing is sucking on a fake penis."

"A gross oversimplification. You're overlooking the fact that this is good practice. And quite the sight to behold..." He mumbled under his breath.

"Yes, practice of the sort which I have been doing for the past hour, now." I growled, though I didn't intend to sound so peeved.

"And I just keep getting harder and harder..." He mumbled to himself.

"What was that?" I pretended not to hear.

"I don't pay you to sass me." He covered. Good save.

"Ugh...whatever. It's not as if you're going to fire me."

"You got that right." He replied shamelessly. Over the course of this past week, I had also learned something interesting. Apparently, Umbra didn't go out of his way to hire any of his whores; they all came to him. However, he was incredibly fond of me. Thus, he chased me down on that one fateful night and practically begged me to take the job. He wouldn't fire me for the world. After he let that slip, I had taken to the habit of teasing him every so often. Sometimes humorous, sometimes bitter. A perfect balance of Cheren which made him go crazy. The odd, white-haired pimp was in love with my looks, my personality...everything! I'm surprised he hadn't just taken advantage of me by now, the creepy fuck.

As I mentally resolved to continue blowing the dildo, Umbra's voice stopped me. "Sooo...if you're so tired of fake cocks...why don't you try your hand at a real one?"

"Huh...where would I get one of those? Do you expect me to just curl up and suck my own dick?" I snickered at the thought, and at my own feigned obliviousness.

"Hmph...as...entertaining as that sounds, you know very well what I was insinuating." He said sternly, and slightly crept up to me.

I smirked. Yes, I knew exactly what he wanted, but I also knew what he DIDN'T want. He wanted me to be afraid, to cower away from him and deny his advances. He was just that kind of guy. So I decided to fuck with him.

With the same boldness and confidence I had developed with my first Pokémon, I quickly crawled up to the white-haired pimp. "What? What were you insinuating? I have no idea, Umbra~." I hummed into his ear. He flinched, surprised by my audacity. Adjusting my positioning, I slid onto his lap and straddled his thighs, grinning wryly. The same smile he had given me on my first day of the orientation. Almost immediately I could feel heat rush to his pale, cold cheeks. "Were you intending to bring in a guy, perhaps? And I could practice on him?"

"Well...no, not when you...already have another man...I-in here.." His voice trailed off and his breathing grew ragged as I nipped and licked the shell of his ear. Wrapping my arms around his built shoulders, I ground my crotch against his raging erection for good measure. Umbra shuddered and hissed. "Ahhh...st-top...fuck, it's not fun if you're not...t-timid."

"Ha! Don't underestimate me, Umbra. I was never timid." I winced, my building tent catching friction as well.

"You…ffuck…were when I first told you how...haaahhh...m-..men fuck other men."

"Hmm...no, maybe 'surprised' is the word you're looking for. Just as you are now~." I noted in a singsong tone, taunting him. My fingers wandered into his tank top, and slipped into his jeans. That hazy look of his was just plain priceless.

When he could finally comprehend what I had said, he furrowed his brows. Combined with his blush, his face seemed to be on fire. "No- Hey! I can't be surprised! I'm a member of the-…er..." He cut himself off, but I interrupted anyways.

"Oh? Heh...that look on your face a few seconds ago could beg to differ." I thrusted against him harder to sabotage his argument.

"Ahh...damn, w-well-"

A sudden vibration of the phone in his pocket shut him up. Managing to ignore how it tastefully tickled my erection, I took the opportunity to tease him again. "Awww...Did you have to put a vibrator in your pants because I got you SO riled up?"

Umbra playfully shoved me off of him, and I bounced back on his mattress. "Arceus, first the teasing, now this? You've become so naughty, Cheren! I've created a monster." He joked, getting up off the bed to remove his phone from his pants' pocket. Upon seeing the caller ID, it seemed, his eyes grew wide. "Hold up, I need to take this."

"Alright, Frankenstein, have fun."

Chuckling slightly, he pressed the call button on his phone, and stepped over to the front of the room (I couldn't help but stare and laugh inwardly as he readjusted the boner in his pants). "Hello." He said into the cellular device. By the formality and brevity of his tone, I could tell it had to be one of his clients.

A short silence followed as he listened to the response. He had his speaker off and was turning away from me, so I couldn't hear a word the caller was saying.

"...Well enough...oh, you do? Ask away." Umbra cocked his head to the side slightly, tuning in to the response. "...why yes, actually. I was just in the middle of orientating him, myself." Shit...they were talking about me. Now I was curious. I sat up straight on the bed, trying to eavesdrop on their conversation. No dice. "...yes, he is indeed," I am what? "Did you want him for the night?" Umbra briefly turned to me with a straight face, eyes flashing with subtle concern. That couldn't be good. "...well, he's cute. Really cute. He's got short hair, glasses, a nice ass...what?...Is he blond- no black-haired, why does that even matter...yes he's white, sweet Arceus, man, what is up with your obsession with skin tones? ...You're such a kinky fuck, man, I don't even know if I should entrust his first time with you." I frowned, confused and mildly frightened. Who was this guy?

The men seemed to be bickering for a while on the phone, Umbra conversing with this man as if they knew each other for ages. Finally, the banter ceased, and the pimp returned to a more business-like mien. "So how much you willing to pay?...Hmm...nah, 20k poke? Are you shitting me, that's probably your hourly salary! Haha...how about 75k?...Hey now, don't be cheap. How often do you get to fuck a virgin? ...Yes, I am one hundred percent sure he's a virgin; he didn't even know which way he swung when I hired him..." I blushed, completely mortified. Fucking Umbra and the way he talked about me...I'd thrash him if his client made fun of me for that. "What? You ever know me to be a liar?...I'm serious, you can make sure of it when you strip him. You gonna take the offer or not-...oh, really?" This time, his sidelong glance was one of astonishment mingled with fear. "...Alright, I'll charge your card. When did you want him?...Tonight? Shit, that's sudden...no, it's fine, I'll send him tonight." I scanned the room for my employer's wall clock. It was a quarter to eleven, damn.

I lowered my gaze. Umbra had taken out a piece of paper, and was scribbling something on it. "Mhmm...alright, got it. He'll be there by eleven thirty...no problem, thanks, man. Heh, enjoy." Umbra hung up the phone, and slid it back into his pocket.

With an audible sigh, Umbra pinched the bridge of his nose. He shook his head. "...I was hoping that spiking up the price would deter him from buying you for the night. But, unfortunately, I was wrong. So whatever you do..." He turned around completely to face me, his silver eyes trembling with trepidation. My blood ran cold. "_Whatever_ you do...do NOT let him fuck you."


	8. Chapter 8

Drastic Measures

Ch.8- Dress up

My pupils dilated. I stood up straight on the bed, panicking on the inside. "W-what?! What do you mean?" I exclaimed.

Umbra sighed, dashing over to his walk-in closet. "I mean..." He began in a stressed tone, fumbling through clothes. "Foreplay, hand jobs, blow jobs- whatever- are acceptable. Him slamming your ass is DEFINITELY not."

I stood up off the bed and followed him, confused. "Why? Isn't that supposed to happen? I mean, I'm not arguing, but that's why he wanted me to be a virgin or something, right?"

"Yes." He sifted through the skimpy nightclothes he has his prostitutes wear before they go to work, pinpointing the (incredibly tacky) Pokémon-print ones.

"So...?"

"Ah, here it is." He said, grabbing a half see-through, half lacy nightgown reminiscent of a Meinshao's coloration. I fumed and backed away from him. Arceus-dammit, I knew that scandalous pimp would make me cross-dress sooner or later!

He plucked the matching eared-hairband, panties (which, of course, had a long Meinshao tail on it) and stockings as well. I shook my head disapprovingly. Tonight was going to be a nightmare to rival those of Darkrai itself. "You're wearing these tonight. I can tell by that disgusted look on your face that you want nothing to do with feminine clothes. Despite that, I believe you may find them incredibly comfortable, and-"

"Doubt it. What do you know about cross-dressing?" I growled.

"A lot. Haven't you already learned not to question my experiences?"

I sighed. "Well...yes, however I truly cannot imagine you in such...compromising situations."

"Oh, come off it. I've been bottom more times than I can count on my fingers. And I've been top just as much. Sometimes, I might even cross-dress ironically in latter position, but either way it's quite nice." He said matter-of-factly, passing me the Pokémon-themed clothes.

I laughed, entertained by the thought of Umbra banging some guy or whatever while wearing a hilariously frilly dress. I didn't want to give him any ideas, though. "Ha, fair enough. So tell me about this guy you *cough* stupidly *cough* set me up with." I began removing my jacket and shirt.

He huffed. "Certainly. I was just fixing to discuss that until I was rudely interrupted." He accused, shooting me a stern glare fit for a Galvantula. I winced as it seared through me. "...Anyways, his name is...well, I suppose I'll relinquish that information only if he wishes. He's bisexual, and has a thing for traps and exotic, feline Pokémon. Meinshao may be a shot in the dark, but, whatever, it's close enough. Just wear the ears; and I'm sure he'd appreciate it since he actually trains one." Umbra paused for a second, probably deciding on how to word his next statement. "On another note, he's...pretty huge, and that's not simply innuendo. Buff, burly, built; although he's generally considerate and kind, in the heat of the moment, he'd probably tear up someone as small as you." I threw my shirt to the bed in restrained fury. I wasn't THAT small! "...Which is why I want his dick to stay away from your ass, under any and all circumstances. And before you say anything, I know I've taught you the proper methods of applying lubricant and avoiding major anal and rectal tears. Nonetheless, this is your first commission, so I know you're not going to get things perfect. _Especially_ if you panic when you see him." He elaborated, watching me strip off my pants and underwear with interest. He had seen me naked already, so I didn't pay any heed to that. "Simply put: don't try to take him."

"Note taken. My problem is, however," I began, concern lining my tongue as I slipped on the skimpy gown, which parted down the middle into transparent fabric. The soft, lacy top of the night shirt (obviously intended for bustier chests) rubbed up against my nipples, still hard from teasing Umbra. I held back a small grunt. "The possibility of rape. What if he comes onto me when I deny him? If he's as strong as you say he is, wouldn't be able to fight him off if he did!" I complained, gesturing my arms as a Magikarp flails. The gown's see-through sleeves, which extended past my arms as does a Mienshao's furry ones, flew every which way.

"Don't worry about it." My boss said with a wave of his hand. "Just tell him I won't allow him to fuck you. If he doesn't listen, just call me and leave. He'll understand, though. Don't be so worried." He assured as I slipped on the dark purple panties and mid-thigh high stockings, mumbling a small "ok." The garments were unbelievably soft and comfortable, rubbing up favorably against my semi-erect penis. My boss noticed how blissful I looked. "Hah, I knew you'd like 'em."

"W-what? I don't like them...shut up!" My cheeks turned a light shade of red as Umbra cupped them with a hand and placed the Mienshao ears on my head. He tied the open slit of the gown together with a dark purple piece of fabric.

"Oh, hush, you little tsundere." Before I could protest, he studied me and continued. "Splendid! You look so utterly fuckable. I don't think your client is going to be able to keep his hands off you." He laughed as I huffed in disgust, petting my head. "I can hardly even do it! Now why does it look like there's something missing? Hmmm…wasn't there something else to this outfit?" He pursed his lips and tapped a finger to his chin.

"No. There was nothing else, you're imagining things." I hissed. "Now let me go meet up with this guy before I'm late-"

"AHA, that's what it was!" He exclaimed excitedly, grabbing my hand and dragging me into the closet. "Purple eyeshadow and lipstick!"

"Oh sweet mother of MEW, get me out of here!"


End file.
